Monitoring apparatus and monitoring system. Provided is a monitoring apparatus including an acquiring unit that acquires information relating to an operation status when an operating body is operated, a determination unit that determines one of plural categories of the operation status, which are classified based on a degree of occurrence of a malfunction of the operating body or a degree of danger of the operation status, to which the information relating to the operation status acquired by the acquiring unit belongs, and an attention calling unit that calls for an attention for an operation of the operating body in a case where the information relating to the operation status is determined to belong to a specific category.